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Cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone → Cyclopropyl-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-methanone

HRID 133540
ノート
印刷プレビュー

反応式

HRID 133540 の反応式
[CH:1]1([C:4]([C:6]2[C:7]([CH3:25])=[N:8][C:9]3[S:10][C:11]4[CH2:12][NH:13][CH2:14][CH2:15][C:16]=4[C:17]=3[C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:5])[CH2:3][CH2:2]1>C1(C=CC2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH:1]1([C:4]([C:6]2[C:7]([CH3:25])=[N:8][C:9]3[S:10][C:11]4[C:16]([C:17]=3[C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=[N:13][CH:12]=4)=[O:5])[CH2:2][CH2:3]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 68896615Cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone

生成物 1

HCID 11508442Cyclopropyl-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-methanone収率 8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 11502Stilbene溶媒

反応条件

温度
150 °C

実験手順

To a stirred solution of 0.46 g (1.32 mmol) cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone in 7 ml diphenylethylene was added 230 mg palladium on charcoal 10%. The mixture was stirred over night at 150° C., and then poured onto ethyl acetate (about 150 ml), and extracted three times aqueous HCl (1M). The combined aqueous phases were basified with K2CO3 until ph=8, and then the product was extracted with ethyl acetate. The combined organic phase were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 1:1) afforded 35 mg (8%) cyclopropyl-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-methanone as a light yellow solid. ES-MS m/e (%): 345 (M+H+, 100).

後処理

  1. additionpoured onto ethyl acetate (about 150 ml)
  2. extractionextracted three times aqueous HCl (1M)
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe combined organic phase were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-aa59d649f886481b9711f5c1699912e0
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07390903B2

反応ノート

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